


The First of Many

by spacegirlstuff



Category: Supernatural
Genre: Alternate Universe - High School, Awesome Charlie Bradbury, Castiel and Gabriel are Siblings (Supernatural), Charlie Bradbury & Dean Winchester Friendship, Charlie Bradbury Ships Castiel/Dean Winchester, Dean Winchester Has a Crush on Castiel, Fluff, Gabriel Ships Castiel/Dean Winchester, House Party, Idiots in Love, M/M, Openly Bisexual Dean Winchester, Young Dean Winchester
Language: English
Status: Completed
Published: 2020-12-16
Updated: 2020-12-16
Packaged: 2021-03-10 17:28:13
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,320
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28110900
Author URL: https://archiveofourown.org/users/spacegirlstuff/pseuds/spacegirlstuff
Summary: “Incoming at 6-o’clock.”Dean hastily turns around, inhaling sharply as his eyes lock with the blue ones of the man approaching him, his hair as messy as always, the dark blue shirt clinging his body in all the right places making him-“Stop drooling,” Charlie elbows him in the stomach making him shoot her an irritated look before looking back at Cas, a wide smile on his face.“Hello, Dean,” Cas says, his gravelly voice making Dean’s stomach flip in ways he didn’t want to think about.“Hey, Cas,” he replies, hoping his voice doesn’t sound as breathy as he thinks it does, “Didn’t expect to see you here.”
Relationships: Castiel/Dean Winchester, Charlie Bradbury & Dean Winchester
Comments: 4
Kudos: 100





	The First of Many

**Author's Note:**

> I wanted to write something more casual and all because I had absolutely no idea for more fluff so well... here it is!

Dean Winchester sits on the bathroom counter, shifting ever so slightly every few seconds, trying to shake off the nerves he was feeling. This would be the first party he would be attending ever since he came out in the middle of the cafeteria two weeks ago in the most embarrassing way. In his defense, it had been a dare from his friend and Dean Winchester never backed out on a dare and so in less than a minute, he was standing on the table shouting about his obsession with western movies and another minute later he was being dragged back by his friends as he tried to beat the shit out of a homophobic asshole.

Everyone else had been surprisingly fine with the knowledge that the freshman heartthrob was bisexual, but tonight was really going to test it.

“Dean, stop moving.” says Charlie, his best friend for what seems like forever but was actually just four years, “Don’t worry, it’s going to be fine.”

“I’m not worrying,” he turns to look at her as she applies chapstick, her red hair down in perfect curls thanks to Dean.

The redhead gives him a sideways glance, making him sigh. “Everyone loves you and you liking dicks is not going to change that,” 

“Because that’s definitely what happened in high school,” he comments, running a hand through his hair.

“Hey!” she swats his arm away from messing the brown strands further, “Don’t touch that masterpiece.”

“Yes, your highness,” Dean rolls his eyes, cursing loudly as he reads the time, “Can you please hurry up?” he asks, “We are more than an hour late.”

“Don’t blame me,” Charlie picks up a tube shaking it before turning to face Dean, “You were the one who almost had a breakdown about which t-shirt to wear with-”

“Okay, I made us late, but can we please leave now before Benny starts to think that someone kidnapped us on our way?”

“Alright,” she sighs, stepping towards the man sitting on the counter, “Close your eyes,” she instructs.

“Why?” Dean questions even as he does as she asks him.

“Because I want you to look drop-dead gorgeous tonight.”

Dean flinches away a bit when he feels something in his eyes before relaxing as Charlie’s warm hand cradles his face gently. This would not be the first time he would be wearing eyeliner, but this would definitely be the first time someone other than Charlie would see him wearing it and he would lie if he said that he was not looking forward to it.

“All done,” the woman says, stepping back to inspect her work as Dean flutters his eyes open slowly to make sure he doesn’t mess it up.

“Let us go, then.” he jumps down from the counter, wiping his sweaty hands on his ripped jeans.

“Yup let’s-” she stops her eyes wide.

“What?” Dean starts, but the read head is already out the door before he finishes the question, “Are we even going to make it to the party before this year ends?”

“Stop being dramatic,” Charlie replies, stepping back into the bathroom with a black leather jacket that he vaguely remembers buying in a thrift store almost six months ago. Handing it out to Dean, she says, “Put it on.”

“Hell no,” he responds, “It’s less than ten out there.”

“Please,” she begs, getting ready to pull the bigger guns out if he refuses, aka the puppy eyes she learned from Sam, “You will look awesome!”

“I’m not going to freeze my balls off just because-”

“Okay, just try it on,” she steps towards him, “If you don’t like it then you don’t have to wear it.”

He eyes her skeptically, “Really?”

“Promise,” 

Dean hesitates a bit before taking the jacket from her hands, his eyes not leaving the redhead. Charlie had never given in for anything this easily and her agreeing with Dean without a fight was making the man nervous. He shakes his head before shrugging on the black leather piece, rolling his shoulders once and humming when he finds that it fits him perfectly and was in fact pretty warm too.

Charlie whistles slowly, making the man look at him, an eyebrow raised as he asks, “What?”

“You look hot,” she says, her eyes wandering over his frame, making him shuffle on his feet as he steps in front of the full-length mirror, Charlie following him with a smirk.

His breath stutters as soon as his gaze lands on his reflection. Charlie had promised him to make him look _drop-dead gorgeous_ for tonight and by god, she had lived up to her word. The white band t-shirt looked perfect with his black ripped jeans his best friend had blackmailed him into wearing, and the black leather jacket he had donned was definitely completing the whole look.

“You win,” he finally says after almost a minute, still staring at his reflection as the redhead smiles in victory.

“Well, pretty boy, let’s get going now.” winks at him in the mirror before walking out of the bathroom. With a deep breath and one last look at his reflection, he follows.

Less than half an hour later, he is sitting in the middle of some random persons living room, a half-empty red cup in his hand, his other arm wrapped around Charlie as they converse with a girl named Anna who looks maybe a bit too interested in him to make him feel comfortable around her.

“He’s here,” Charlie leans up whispers in his ear.

“Who?” Dean questions even when he knows exactly whom the redhead is talking about.

“The man of your dreams,” she replies.

“I don’t know what you are-”

“That man with the _messy black hair_ that makes you feel like running your fingers through it every time you look at it.” Dean groans as the redhead repeats the words he had said one night after a little too much vodka, “And those _plush pink lips_ that make you want to drag him into an empty classroom and kiss him until he doesn’t remember anything other than your name.” Not to forget those perfect baby blue eyes that make you weak in your knees, stuttering like a teenager every time he as much as-”

He puts a hand on her mouth to effectively shut her up, looking away as he tries to control the blood rushing to his face. 

“Sounds like someone's got a crush,” Anna says, making both him and Charlie stiffen.

Dean shoots his best friend a look that promises revenge, the redhead mouthing ‘Sorry’ before he turns back towards Anna with a smile. “Not exactly,” he replies, “Just someone whom I think looks good,”

“It’s Castiel, isn’t it?” she inquires with a pause, making Dean gulp before nodding briefly.

“Is it that obvious?” 

“Honestly, it is.” she answers with a smile, “But, if it makes you feel better, I realized it because I do know what my brother looks like.”

Dean gapes at her, the girl emitting a laugh at his reaction. Anna stands up, patting his shoulder softly, “Make a move,” she whispers near his ear, bending down to be audible clearly, “You might be surprised with what you find out.”

He can only nod in response as both of them watch her walk away, Charlie whipping her head towards him as soon as the other girl disappears, the look in her eyes making Dean regret ever agreeing to come to the party.

“Whatever you are thinking, just don’t,” he says.

“You don’t even know what I’m thinking,” She replies, twisting in her seat to scan the crowd.

“I really don’t-,” 

Charlie ignores him, instead, getting up from the sofa and dragging him up behind her towards the kitchen.

“Where are you taking me?” Dean questions, shooting his best smile towards the group of girls he just bumped into.

“You need a refill,” the redhead maneuvers her way past the hallway and into the kitchen, which was thankfully less crowded than the living room.

“My cup is not even empty yet,” He says only for the woman to turn around and snatch the red cup from his hand, drinking it in one go.

“Now it is,” she grins at the exasperated look on his face, her eyes widening when they land on something over his shoulder, “Incoming at 6-o’clock.”

Dean hastily turns around, inhaling sharply as his eyes lock with the blue ones of the man approaching him, his hair as messy as always, the dark blue shirt clinging his body in all the right places making him-

“Stop drooling,” Charlie elbows him in the stomach making him shoot her an irritated look before looking back at Cas, a wide smile on his face.

“Hello, Dean,” Cas says, his gravelly voice making Dean’s stomach flip in ways he didn’t want to think about.

“Hey, Cas,” he replies, hoping his voice doesn’t sound as breathy as he thinks it does, “Didn’t expect to see you here.”

“I wasn’t planning to buy Gabriel barged into my dorm declaring that I am his designated driver tonight and-”

“Hello, Dean-o” Gabriel appears behind Cas, his eyes traveling down Dean’s body with an appreciative look, “Woah,” he says, “You might just become my bi awakening.”

“Ignore him,” Castiel rolled his eyes, turning back towards Dean and Charlie, “I heard that they are starting a campfire in the backyard. Do you want to come?”

“Hell yeah,” Dean answers,, “Let me just refill-”

Charlie plucks his glass from his hand, looking at the black-haired boy, “Why don’t you both go and make sure they have some space for us while Gabe and I can grab a refill,”

“That sounds great!” Castiel smiles at her, “Thank you.”

“Anything,” Dean internally groaned as soon as he caught the grin creeping on his best friend’s face, “You want a beer or coke?”

“Coke would be fine,”

“Alright then!” She grabs Gabriel’s forearm, dragging him away from the duo with a hardly concealed wink towards Dean.

“So,” Dean looks over at Cas, “Let’s get going.”

“Lead the way,” the man replies with a gesture towards the patio door.

Trudging through the sea of bodies Dean makes his way across the room at a slow pace, his heart rate increasing drastically when Castiel puts his hand on his back to steady him as he stumbled over a misplaced bottle of vodka on the floor, the warmth of the man’s hands under his jacket, his fingers burning through the fabric of his t-shirt and into Deans skin.

“Careful,” Castiel whispers near Dean’s ear, making the hair on his neck stand.

“Thanks,” Dean mumbles back, continuing forward, and if Castiel feels Dean lean back slightly into his hand, he doesn’t comment on it.

As they step outside the glass door, Dean hums in appreciation as the cold November air nips his skin, finally away from all the sweaty bodies and the smell of alcohol and too much perfume. Castiel shivers slightly next to him, making Dean turn towards him with eyebrows raised. 

“Will you be fine?” Dean asks concernedly when he realizes that the man is only wearing a t-shirt.

“Yeah,” Castiel answers, rubbing his hands down his arms looking towards the firepit and the bunch of blankets stacked a few feet away, “But let’s get into a blanket before I turn into a popsicle.”

“Of course,” he smiled, walking towards the pile of duvets to pick up the thickest one he can find, and then returns back next to Castiel, sitting on the log next to the man as he carefully drapes the quilt over his shivering body.

Castiel looks at him with a grateful smile, wrapping the grey blanket over him tightly and snuggling into it in a way that made Dean’s heart flutter.

“You look different,” the dark-haired man says after a few seconds.

“Is it a good difference or a bad one?” Dean questions, blaming the heat of the fire for his sweaty hands.

“A good one,” Castiel replied, his gaze catching Deans, “I like it.”

“Thank you,” Dean turns towards the fire, not even trying to fight the blush creeping onto his cheeks.

Almost two minutes later, when he can still feel the man’s eyes on his face, he says, “I didn’t know that Anna was your sister,”

Castiel sighs, finally looking away, “I have a messy family.”

“Okay,” he prompts the man to continue, shuffling towards him slightly when the air starts to get a bit cold.

“It’s nothing interesting,” the dark-haired man says, “I don’t want to bore you.”

“You won’t,” Dean nudges the other man’s shoulder with his own, “I just wanna know more about you.”

Castiel looks at him with a blinding smile, making Dean’s lips tug up in response. Castiel picks up an end of the blanket when he sees him shiver, silently gesturing towards him to come closer so they both can share it. Dean hesitates a second before crawling under the warm quilt, rolling his eyes at the wolf whistles from his friends and doing his best to ignore the way his heart races as he sits next to the guy who has been visiting him in his sleep a lot more nights than Dean would admit, sinking into the warm body next to him, sighing softly when he feels Castiel’s arm wrap around his waist, pulling him closer.

“My family is not very interesting,” Castiel starts, Dean listening with rapt attention as the rest of the world fades away.

And if he chooses to ignore a certain someone shouting ‘Get a room!’ towards them with the redhead next to him shooting a sly smile towards the pair, he decides to forgive them because if those two had not left them alone then Dean knows that he definitely wouldn’t be going home tonight with a new number in his phone and the promise of a proper date next weekend.

**Author's Note:**

> Hope you liked it!!!  
> You can find me on tumblr at [spacegirlstuff](https://www.tumblr.com/blog/spacegirlstuff).


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